| 1999-12-28 | WolvesvNorwichChampionship · England | 1–0 | Championship · England |
| 1999-12-26 | StockportvWolvesChampionship · England | 3–2 | Championship · England |
| 1999-12-17 | WolvesvBirminghamChampionship · England | 2–1 | Championship · England |
| 1999-12-14 | CrewevWolvesChampionship · England | 1–0 | Championship · England |
| 1999-12-03 | WolvesvMan CityChampionship · England | 4–1 | Championship · England |
| 1999-11-27 | TranmerevWolvesChampionship · England | 1–0 | Championship · England |
| 1999-11-24 | IpswichvWolvesChampionship · England | 1–0 | Championship · England |
| 1999-11-20 | WolvesvSwindonChampionship · England | 1–1 | Championship · England |
| 1999-11-06 | WolvesvGrimsbyChampionship · England | 3–0 | Championship · England |
| 1999-10-31 | West BromvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-10-26 | WolvesvSheffield UnitedChampionship · England | 1–0 | Championship · England |
| 1999-10-23 | WolvesvPort ValeChampionship · England | 2–2 | Championship · England |
| 1999-10-19 | FulhamvWolvesChampionship · England | 0–1 | Championship · England |
| 1999-10-16 | BarnsleyvWolvesChampionship · England | 1–2 | Championship · England |
| 1999-10-09 | WolvesvBoltonChampionship · England | 1–0 | Championship · England |
| 1999-10-03 | WolvesvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-09-28 | Crystal PalacevWolvesChampionship · England | 1–1 | Championship · England |
| 1999-09-25 | Sheffield UnitedvWolvesChampionship · England | 3–0 | Championship · England |
| 1999-09-19 | Nott'm ForestvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-09-11 | WolvesvHuddersfieldChampionship · England | 0–1 | Championship · England |
| 1999-08-28 | WolvesvWalsallChampionship · England | 1–2 | Championship · England |
| 1999-08-21 | QPRvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-08-14 | WolvesvPortsmouthChampionship · England | 1–1 | Championship · England |
| 1999-08-08 | Man CityvWolvesChampionship · England | 0–1 | Championship · England |
| 1999-05-09 | WolvesvBradfordChampionship · England | 2–3 | Championship · England |
| 1999-05-04 | GrimsbyvWolvesChampionship · England | 0–0 | Championship · England |
| 1999-04-30 | BoltonvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-04-25 | WolvesvWest BromChampionship · England | 1–1 | Championship · England |
| 1999-04-17 | BirminghamvWolvesChampionship · England | 0–1 | Championship · England |
| 1999-04-10 | WolvesvCrystal PalaceChampionship · England | 0–0 | Championship · England |
| 1999-04-05 | Sheffield UnitedvWolvesChampionship · England | 1–1 | Championship · England |
| 1999-04-03 | WolvesvPortsmouthChampionship · England | 2–0 | Championship · England |
| 1999-03-30 | WolvesvCreweChampionship · England | 3–0 | Championship · England |
| 1999-03-20 | BarnsleyvWolvesChampionship · England | 2–3 | Championship · England |
| 1999-03-16 | BuryvWolvesChampionship · England | 0–0 | Championship · England |
| 1999-03-13 | WolvesvBristol CityChampionship · England | 3–0 | Championship · England |
| 1999-03-06 | QPRvWolvesChampionship · England | 0–1 | Championship · England |
| 1999-02-27 | WolvesvHuddersfieldChampionship · England | 2–2 | Championship · England |
| 1999-02-20 | SunderlandvWolvesChampionship · England | 2–1 | Championship · England |
| 1999-02-13 | WolvesvPort ValeChampionship · England | 3–1 | Championship · England |
| 1999-02-06 | WolvesvOxfordChampionship · England | 1–1 | Championship · England |
| 1999-01-30 | StockportvWolvesChampionship · England | 1–2 | Championship · England |
| 1999-01-16 | WolvesvWatfordChampionship · England | 0–0 | Championship · England |
| 1999-01-08 | TranmerevWolvesChampionship · England | 1–2 | Championship · England |